Twenty-five years ago, hip-hop had a surprisingly momentous month. No less than four classic albums dropped in November 1993, including two debuts that would change hip-hop forever: Wu-Tang Clan’s Enter the Wu-Tang (36 Chambers) on Nov. 9 and Snoop Dogg’s Doggystyle on Nov. 23. In addition, A Tribe Called Quest released its third (and arguably best) album, Midnight Marauders (Nov. 9) and Queen Latifah released her third album, Black Reign (Nov. 16). Incredibly, each of these four albums represented a different style of hip-hop.

Following the success of Dr. Dre’s The Chronic in 1992, which introduced Snoop Doggy Dogg to the world, Doggystyle cemented West Coast hip-hop’s status as a distinct style that was no longer content to take a backseat to the New York originators. Of course, five years earlier, N.W.A. had taken the world by storm with Straight Outta Compton, but until The Chronic, there wasn’t a sense that the West Coast could truly compete with New York in terms of success and popularity.

The late 1980s and early 1990s were a pioneering time for West Coast hip-hop, with the emergence of not only Dr. Dre, Eazy-E, and Ice Cube, but also Tupac Shakur, Ice-T, Digital Underground, Too Short and MC Hammer. By the time Doggystyle came out, Dr. Dre’s G-funk sound had come to define the West Coast, and Snoop’s first album was a natural extension of the songs he had anchored on The Chronic. His laid-back, sing-songy style was totally unique at the time and, although sexism was nothing new in hip-hop, Doggystyle took misogynist and sexually explicit lyrics to a new level. And of course, there has never been a greater weed connoisseur than Snoop, who was likely the first rapper to so openly publicize his love of the herb.

One could hardly imagine a style more distinct from Doggystyle than Wu-Tang’s debut album, with its dark, grimy sound and obscure kung-fu and Five Percenter references. Many critics viewed Wu-Tang’s debut album as a response to The Chronic and the fact that West Coast hip-hop had become commercially successful. A Rolling Stone piece states: “RZA has claimed that the album’s low-end attack was his attempt to outdo the deep bass work that Dr. Dre employed on his melodious The Chronic album the year prior.”

A few weeks ago, Wu-Tang released a mini-film reflecting on the group’s debut album, called For The Children: 25 Years of Enter The Wu-Tang (36 Chambers). In a recent interview, RZA stated, “If you take our first single, ‘Protect Ya Neck,’...we all had relatable, evergreen ideas that—for anyone digging and dissecting our work—will find that these lyrics stand the test of time...That reflection of that pure, unfiltered, untouched by saccharine corporatized hip-hop.”

Indeed, GZA’s anchor verse on Wu-Tang’s signature song—perhaps one of hip-hop's best posse tracks ever—is one of the most lyrically brilliant critiques of the commercialization of hip-hop: “First of all, who’s your A&R/A mountain climber who plays an electric guitar?/But he don’t know the meaning of dope/When he’s looking for a suit-and-tie rap that’s cleaner than a bar of soap.” It’s hard to overstate the impact of Enter the 36 Chambers, especially because Wu-Tang’s model of a cohesive group that was also able to accommodate solo careers has rarely been repeated. RZA’s production technique was particularly influential, as he produced not only most of the debut solo albums of Method Man, GZA, Ol’ Dirty Bastard, Raekwon, and Ghostface Killah, but in later decades, tracks by Jay-Z and Kanye West.

A Tribe Called Quest’s influence is equally difficult to quantify. Some believe the group released its best album with 1993's Midnight Marauders. You would be hard-pressed to find a better follow-up to the group’s widely acclaimed second album, Low End Theory, a feat possibly repeated only by OutKast with ATLiens and Aquemini. With the infectious singles “Award Tour” and “Electric Relaxation,” it was clear that Ali Shaheed Muhammad was one of the best producers in the hip-hop game. And while Phife Dawg had previously been in the shadow of Q-Tip, his verses on Midnight Marauders were the standouts, like his memorable line from “Electric Relaxation”: “I like ‘em brown, yellow, Puerto Rican and Haitian/Name is Phife Dawg from the Zulu Nation.”

Both A Tribe Called Quest and Queen Latifah were members of the Native Tongues collective, so there were clear similarities in their styles, particularly their use of jazz samples, their espousal of Afrocentrism, and their relatively upbeat and empowering lyrics. This is especially apparent if you compare their lyrics to the dark musings of Wu-Tang and the nihilism and hedonism associated with gangsta rap, as represented by Snoop Dogg. But there were important differences too. Phife and Q-Tip tended more toward wordplay and innovative braggadocio, while Queen Latifah put forth a distinctly Black feminist stance.

Black Reign as an album doesn’t approach the brilliance of Midnight Marauders or Enter the 36 Chambers, and yet it’s the only one of these four albums that won a Grammy, for the groundbreaking single “U.N.I.T.Y.”; interestingly, the song beat out Snoop Dogg’s “Gin and Juice,” which was also nominated. Building on her 1989 hit with Monie Love, “Ladies First,” “U.N.I.T.Y.” was arguably the first hip-hop song to explicitly address misogyny within the genre and gender-based violence in general. Queen Latifah takes on a defiant tone—both vocally and in the song’s video—with the mantra running through the song, “Who you callin’ a bitch!” and the chorus urging women to call out misogyny: “You gotta let him know/You ain’t a bitch or a ho.” Although Queen Latifah wasn’t the first prominent female rapper, she was certainly the most explicitly feminist MC, consistently linking the empowerment of women with Black liberation struggles.

Given these four very different albums, it must be asked: Why was November 1993 such a fruitful moment for hip-hop? The obvious answer is that the genre was maturing and branching off into sub-styles following its crossover success, as exemplified by the “Walk This Way” rap-rock collaboration in 1986 between Run-DMC and Aerosmith. By the later 1980s, hip-hop artists had seen that their music could be commercially successful and that they could realistically aspire to having a career in hip-hop.

Of course, hip-hop’s crossover provoked complex reactions: While being able to support yourself practicing your craft was a good thing, artists were well aware of the history of White appropriation of Black popular music and knew the same thing could happen in hip-hop. This coincided with a renaissance in Black nationalist and Afrocentric ideology, which was incredibly influential for hip-hop and resulted in a sub-style called “message rap,” as espoused by Public Enemy, KRS-One, the Native Tongues collective, and many others. One of the main threads running through this style was a critique of commercialism and the feeling that hip-hop was being watered down to appeal to White audiences, which is clearly seen in Wu-Tang’s philosophy.

There were other contradictory trends going on in hip-hop in 1993. On the one hand, there was rampant misogyny, not only in “gangsta rap,” but in the more insidious sexism and homophobia of certain Black nationalist groups like Brand Nubian, who categorized women in one-dimensional ways as either a “queen” or a “ho,” and not as complex human beings. On the other hand, there were MC’s like Queen Latifah challenging sexist stereotypes, or—like MC Lyte and Salt-N-Pepa—simply proving they could rap just as well as men could. These women set the stage for an explosion of incredible female MCs in the mid-late 90s, like Lauryn Hill, Da Brat, Lil Kim, Missy Elliott and Foxy Brown.

Looking back on the state of hip-hop 25 years ago, the genre’s stylistic diversity is what jumps out. Many a hip-hop purist looks back on the 1990s as the “golden age,” when even more commercially oriented artists had a strong foundation in the roots of hip hop. However, musical styles can never remain static; they have to keep evolving or they die. So while some Generation Xers might thumb our nose at the current state of hip-hop, they can always take refuge in revisiting our favorite jams from a generation ago. Whether it’s “Gin and Juice,” “U.N.I.T.Y.,” “Shame On A Nigga,” or “Electric Relaxation,” these four albums have stood the test of time. —Rebecca Bodenheimer